US2234581A - Hydrocarbon composition containing organic boron compounds - Google Patents

Description

Patented Men-11 "*jiYfazsatsi'" v .nmnocaimoncomosmon comma v .ionqamonoaomcomounnsq I ;m iieeinoe beutmm 'ne t stu "3 ardoilneyelopment Company,acorporation I Noni-am A "Application September so, long. 8eeialNo.l6o,621 I I Y A. The present invention improyedoil flammable. mnammee; mealtime, compositions and more particularly toimproved purelyorgano compoundathatis the coma lubricatinlollsand pounds in which boronis-connectedonlyto hye a oraaniceompoundsotboron. I p drocarboni radicalsr pi the, purely-orzanobo- I ,Ofls used tor, the lubrication ot'internal com rincs, the aryl derivatives vand especially those bustion engines and for otherservices'involyin: which substantially inm w c m4? v r exposure-to. high temperaturesand airor comnaphthyl borine .are preferred iorthe purposeof 7 V. v bustion gases are subjected to severe oxidizin: thisinvention. 'Ihistendency otthe organo bo conditions. y j c I a .rinee tooxidize isareatlyreducedwhentheyare 1o ;Itiis an obieet o t this invention to improy'e coordinatedwith a auitlble oompoundsuchias lubricating cjompositionsrand mineral oil comammonia 'or'anamine' or :with :ionic. Iroups such positions generally by rthe .additionthereto oi as the OH ion orthe fluoride ionr; Examplesvoi organic compounds, of boron. ln isuch cointheresultingcoordinatedorgano boron complexes .pounds. h boi' nce m iai d ir so-g c r a. I lii least one carboniatom Other-and urther o r cm VI u iectsof thisinvention will be apparentirom the by following descriptipnmdithecmm. i h I In these compounds boron is preferably, at- ,1 a fi d d m $1 w e e vwimmm triphenyl I II I 7 2o m m icimnac'enmm tfiph'enyl borine ethymmme. 23 1' drogenalso attachedtocarbonbutmay inaddi- I I II i w tion'contain'other elements such as nitrogen, oiy- 'i d mun s 0' 3 1 bmonffl a gen, sulfur, chlorine. andthe like, orin general compound! are m lfi flu 1n the' qw I may contain various 'non 'metallic elementsin m m wed li id prci'erredqfor the I Laddition' tohydrogen and carbon; l 9 imposes on account of-their greater 25 I the ma n onfoi the ml nd8,$ W aum sreatereeee meani the ,a mplealkyl hydrocarbon radicals maybe m o s-ma a n 9 lrtheffl I used} such as ethyl} methyl, propyl, but'yl, and? the va ence: ll' v m cd wi h elements other. than 1 like, whetherstreight chained or branch chained, c bon. 3 for cxamplc-nitrosen, oxygen, sulfur I and thcse"are satisiac'tory'particularly athigh -1 8m. fle also muchmore atablewithre 3 11 I temperatures, say 200 0.; 2501'- c.. -,.a d ihizh'er. p o ox i tion in airlthan are the trialkyland;. I "(The cyclic radicalssuchas-phenyL'naphthyLantrim! borines. ,flhe most-i'amiliar examples of thryl; are "of much mpounds of. typg....ar the aminoflalbl I I they have a greater ra seoteii'cctiveness both at end-amino W D acids. Oth ll'isuchucomy I V lowtemperatures, 100 0,; to 150" icgfsnd-ni h. no nds' rediphmlbom c o i ph yl omn 35 I j temperatureairom 200 'C. .to' 250?'C.', a ny1 9 cn d (ClHs):B]aS.",. V'Ihealkylatedaromatic radicala'otwhich tolyl; p c mnd ng alkyl compounds. v alpha" and beta normal or. isopropyl-naph hyl, the alkyl andaryiboricfacids, such as n-propyl v primary or secondary hexyknaphthyl t th acid, isobutyl boric acid; isoamyl borlc acid, I u 0 compounds may be w e e, gr, espe; and phenyl boric acid may be used. However-. cially desirable but the arylsubstituted 111mm; a the low solubilityin hydrocarbon solvents oith i I such a diphenyl methane also satisfacto compounds renders themv less desirable !or this In some cases it is preferred to use the me h the coordinated l xes mentioned aromatic compounds to the unalkylated in n above. v u to obtain a greater solubility, although it must While the exact a u e of se various .com- I b ppreciated that the substances 01 this clans P nds and the mechanisms by which they 1 I v w areordinarilyfreely soluble in hydrocarbon prove e l ng o l re-not articularly and likewise that they areused in very miniite erstood, it is observed that they appear-tot A a quantities. a I show in sreateiyor less decree heli m ty 0 I I so In these organicboron compounds all the or-' d fl lnl 1 81 t ndency of the 011.1

sanic radicals may be similar or they may be dii-r which means-that decomposition products formed I p ierent, and one or more valences orboron may wundertheir influence, whatever their nature, are also be attached. to hydrogen atoms. Y tor the mostpart .freely soluble or,atleast. dis- Many organo boron compounds arereadily oxipersible in the oil and thatthetendency' toward l6 dined in air, some even being spontaneouslyinpreclpitationisthussreatiydiminished,' g s5 I I No explanation oi-this behavior is presented and it should benoted that all show decrease in sludge Iormingtendency of oils which ordinarily produce a substantial quantity of sludge. It is much a's-.50% i re ir d; 1. I

not desiredtoini'er from the above. that sludge formation {is theresult of oxidation alone as is sometimes thought and His specifically desired not tolimit the present invention to any theory or the chemical action involved.

In the above description, several organo-boron compounds are mentioned andthesuitable ,alkyl,

or aryl groups are also given. From this it will be clear that any combination of boron with any oi the radicals of the organic groups are satisfactory for the present purposes.

The amounts 0! the agents'which are are in all cases minute, as muchlas .01 or .02% producing noticeable eflects. It is generally desirable, however, to use 0.2% and it is rare that as The substances mentioned above 'are effective in many different ftypes oi petroleum products, having boiling points above kerosene irrespec I -tive of the type or source, whether'derived from paraflln or napht enic or the various mixed base crudes and 'whetherrefined by acid, clay',1s0lvent extraction, hydrogenation, destructivehy drogenation or otherwise, including the white oils'reflned' to 'a high degreewith strong or concentrated sulphuric acid. As noted above, one

of the principal propertiesot-these boron compounds is their eiilcacy in" reducing-tendency to sludgin'g, but it will be realized that in no ease is this tendency absolutely eliminated, and it is in many cases desirableto add; substances of the I class of sludge dispersing agents totheoil-comlustration of this invention positionseontaining the boron compounds.

The eflectiveness of the organo-boron compounds in lubricating oilsis indicated by the following example, which is presentedonly as an 11- and is not intended tolimititin any wa yz j 1 Example l A blank sample oi a well-refined lubricating oil, S. A. E. 50, was comparedina series of tests with a sample oi-the same oil to which was added 0.2% of triphenyl :b'orine' ethylamine. The results are indicated in the following tablez standardized dimensions which is held at 250 C. The amount reported is in milligrams.

I. A lubricant ganic group o! the class 'oi CL OH. O and B.

3. Composition oifmatterjc'omprising ahydroually circulating air through a 10 cc. sample of the oil at 200 C. and a constant rate and-deter mining at 15-minute intervals the amount absorbed as cc. of oxygen.

, The cone (test which isioundtobest accord 5 with ordinary operations-represents the naphtha insoluble residue produced in 2 hours time when v the oil is allowed to flow at a rate of 30 cc. per

hour around agroove cut in an iron cone oi l From the above table it will be seen that the addition "agent improved the'oil decidedly by reduction of jthe-o ddation rate and by the cone test. 1 y

"' "The present invention is not limited to any particular addition agents, nor to anytheory oi the eitect or these substances, nor to the particu-' H lar amounts but only the following claims.

*I'clalm": 1 I 20 comprising in combinationa major proportion 01- a hydrocarbon oil; and a minor proportion oi'an organicboron-comp'ound, said compound containing atleast one carbonborofi-bohdi a. 2s- 2. Composition oi matter comprising ahydrocarbon 011 containing in solution a minor proportion of an organo-boron compound of boronin which the boron is Joineddirectly to acarbon atom'of anorganic group and 'also to anfinorc'arbon oil containing i'nfsl'alution a minor proportion of an organo-boron compound o!'boron" in which the-boron is joined directly to a carbon atom oi an organic group, said compoundaisobeingcoordinated with a nitrogen base. 1

" 4. A lubricant comprising in combination a v 'major' proportion of a viscous hydrocarbon oil and a minor proportion of triphenyl borineethyl d.

amine.

5, A lubricant compris ng," in common a major proportion or, a hydrocarbon oil and a minor'proportion oi a'tri-phen'yl boron compound.

, as. Composition according to claim '2 in which 4s" said hydrocarbon oil'is a well-refined lubricating 7. Composition-of matter comprising'lfin comblnation a major proportion'oi a hydrocarbon oil 1 anda minor. proportion oi an organic boron].v compound; said compoundgjcontaining at least 'one 08- 7 0n-boronbond. I

8. Composition oi matter comprising a hydrocarbon 'Oil-containingfin solution a minor proportionioi atri-aryl boron compound.